Synthesis of -Tetrafluoro(trifluoromethyl)-λ-sulfanyl (CFSF)-Containing Olefins via Cross Metathesis.

The cross-metathesis reactions of -tetrafluoro(trifluoromethyl)-λ-sulfanyl (CFSF)-containing olefins expand the repertoire of synthetic transformations of CFSF-substituted molecules. Treatment of a primary alkene and 3-CFSF-propene with a second-generation Hoveyda-Grubbs catalyst yielded the cross-metathesis product in good yield under very mild conditions (room temperature). CFSF-propene undergoes cross metathesis with substrates containing electron-withdrawing groups or electron-donating groups at room temperature or under dichloromethane reflux. The formation of the CFSF-propene homodimer and the utility of that dimer to undergo selective cross-metathesis reactions are described.